Iron(III) and Zinc(II) calixarene complexes: Synthesis, structural studies, and use as procatalysts for ε-caprolactone polymerization

Chemistry - An Asian Journal

Volumn 5, Issue 3, 2010, Pages 621-633

  Arbaoui, Abdessamad ^a   Redshaw, Carl ^a   Elsegood, Mark R J ^b   Wright, Victoria E ^b   Yoshizawa, Akina ^b   Yamato, Takehiko ^c  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c SAGA UNIVERSITY   (Japan)

Author keywords

Calixarenes; Crystal growth; Heterometallic complexes; Iron; Polymerization

Indexed keywords

ALKOXIDES; CALIXARENE COMPLEXES; CALIXARENES; CAPROLACTONE; CAPROLACTONE POLYMERIZATION; HETEROBIMETALLICS; HETEROMETALLIC COMPLEXES; MINOR PRODUCTS; STRUCTURAL STUDIES;

CRYSTAL GROWTH; CRYSTALLIZATION; GRAIN BOUNDARIES; IRON COMPOUNDS; METALLIC COMPOUNDS; PHENOLS; POLYMERS; SODIUM; SYNTHESIS (CHEMICAL); ZINC; ZINC COMPOUNDS;

RING OPENING POLYMERIZATION;

CALIXARENE; CAPROLACTONE; HEXANOIC ACID DERIVATIVE; IRON; LACTONE; ORGANOMETALLIC COMPOUND; POLYMER; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CALIXARENES; HEXANOIC ACIDS; IRON; LACTONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYMERS; ZINC;

EID: 77749339880     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900514     Document Type: Article

References (127)

1. Magnesium-based systems: M.-L. Shueh, Y.-S. Wang, B.-H. Huang, C.-Y. Kuo, C.-C. Lin, Macromolecules 2004, 37, 5155.
2. T.- L. Yu, C.-C. Wu, C.-C. Chen, B.-H. Huang, J. Wu, C.-C. Lin, Polymer 2005, 46, 5909.
3. L. F. Sánchez-Barba, D. L. Hughes, S. Humphrey, M. Bochmann, Organometallics 2006, 25, 1012.
4. L. E. Breyfogle, C. K. Williams, V. G. Young, M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2006, 928.
5. Y. Sarazin, R. H. Howard, D. L. Hughes, S. M. Humphrey, M. Bochmann, Dalton Trans. 2006, 340.
6. W.-Y. Lee, H.-H. Hsieh, C.-C. Hsieh, H. M. Lee, G.-H. Lee, J.-H. Huang, T.-C. Wu, S.-H. Chuang, J. Organomet. Chem. 2007, 692, 1131.
7. Calcium-based systems: Z. Zhong, M. J. K. Ankoné, P. J. Dijkstra, C. Birg, M. Westerhausen, J. Feijen, Polym. Bull. 2001, 46, 51.
8. Z. Zhong, P. J. Dijkstra, C. Birg, M. Westerhausen, J. Feijen, Macromolecules 2001, 34, 3863.
9. Z. Zhong, S. Scneiderbauer, P. J. Dijkstra, M. Westerhausen, J. Feijen, Polym. Bull. 2003, 51, 175.
10. Aluminium-based systems: C. Jacobs, P. Dubois, R. Jerome, P. Teyssie, Macromolecules 1991, 24, 3027.
11. A. Duda, S. Penczek, Macromolecules 1995, 28, 5981.
12. A. Kowalski, A. Duda, S. Penczek, Macromolecules 1998, 31, 2114.
13. P. A. Cameron, D. Jhurry, V. C. Gibson, A. J. P. White, D. J. Williams, S. Williams, Macromol. Rapid Commun. 1999, 20, 616.
14. C.-H. Huang, F.-C. Wang, B.-T. Ko, T.-L. Yu, C.-C. Lin, Macromolecules 2001, 34, 356.
15. H.-L. Chen, B.-T. Ko, B.-H. Huang, C.-C. Lin, Organometallics 2001, 20, 5076.
16. R.-C. Yu, C.-H. Hung, J.-H. Hung, H.-Y. Lee, J.-T. Chen, Inorg. Chem. 2002, 41, 6450.
17. M.-L. Hsueh, B.-H. Huang, C.-C. Lin, Macromolecules 2002, 35, 5763.
18. D. Chakraborty, E. Y.-X. Chen, Organometallics 2002, 21, 1438.
19. C.-T. Chen, C.-A. Huang, B.-H. Huang, Dalton Trans. 2003, 3799.
20. L. M. Alcazar-Roman, B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2003, 3082.
21. J. Lewiński, P. Horeglad, E. Tratkiewicz, W. Grzenda, J. Lipkowski, E. Kolodziejczyk, Macromol. Rapid Commun. 2004, 25, 1939.
22. J. Lewiński, P. Horeglad, M. Dranka, I. Justyniak, Inorg. Chem. 2004, 43, 5789.
23. C.-T. Chen, C.-A. Huang, B.-H. Huang, Macromolecules 2004, 37, 7968.
24. N. Nomura, T. Aoyama, R. Ishii, T. Kondo, Macromolecules 2005, 38, 5363.
25. A. Amgoune, L. Lavanant, C. M. Thomas, Y. Chi, R. Welter, S. Dagorne, J.-F. Carpentier, Organometallics 2005, 24, 6279.
26. A. Amgoune, L. Lavanant, C. M. Thomas, Y. Chi, R. Welter, S. Dagorne, J.-F. Carpentier, Organometallics 2005, 24, 6279.
27. J. Lewiński, P. Horeglad, K. Wójcik, I. Justyniak, Organometallics 2005, 24, 4588.
28. S. Milione, F. Grisi, R. Centore, A. Tuzi, Organometallics 2006, 25, 266.
29. M. R. Ten Breteler, Z. Zhong, P. J. Dijkstra, A. R. A. Palmans, J. Peeters, J. Feijen, J. Polym. Sci. Polym. Chem. Ed. 2007, 45, 429.
30. S. Dagorne, F. Le Bideau, R. Welter, S. Bellemin-Laponnaz, A. Maisse-François, Chem. Eur. J. 2007, 13, 3202.
31. M. Bouyahyi, E. Grunova, N. Marquet, E. Kirillov, C. M. Thomas, T. Roisnel, J.-F. Carpentier, Organometallics 2008, 27, 5815.
32. W. Yao, Y. Mu, A. Gao, W. Gao, L. Ye, Dalton Trans. 2008, 3199.
33. M. Bouyahyi, E. Grunova, N. Marquet, E. Kirillov, C.M. Thomas, T. Roisnel, J.-F. Carpentier, Organometallics 2008, 27, 5815.
34. Titanium-based systems: D. Takeuchi, T. Nakamura, T. Aida, Macromolecules 2000, 33, 725.
35. A. J. Chmura, M. G. Davidson, M. D. Jones, M. D. Lunn, M. F. Mahon, Dalton Trans. 2006, 887.
36. Y. Takashima, Y. Nakayama, T. Hirao, H. Yasuda, A. Harada, J. Organomet. Chem. 2004, 689, 612.
37. A. J. Chmura, M. G. Davidson, M. D. Jones, M. D. Lunn, M. F. Mahon, A. F. Johnson, P. Khunkamchoo, S. L. Roberts, S. S. F. Wong, Macromolecules 2006, 39, 7250.
38. Iron-based systems: B. J. O'Keefe, S. M. Monnier, M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2001, 123, 339.
39. B. J. O'Keefe, L. E. Breyfogle, M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2002, 124, 4384.
40. V. C. Gibson, E. L. Marshall, D. Navarro-Llobet, A. J. P. White, D. J. Williams, J. Chem. Soc. Dalton Trans. 2002, 4321.
41. D. S. McGuinness, E. L. Marshall, V. C. Gibson, J. W. Steed, J. Polym. Sci. Polym. Chem. 2003, 41, 3798.
42. M.-Z. Chen, H.-M. Sun, W.-F. Li, Z.-G. Wang, Q. Shen, Y. Zhang, J. Organomet. Chem. 2006, 691, 2489.
43. Zinc-based systems: M. D. Hannant, M. Schormann, M. Bochmann, Dalton Trans. 2002, 4071.
44. D. Chakraborty, E. Y.-X. Chen, Organometallics 2003, 22, 769.
45. H.-Y. Chen, B.-H. Huang, C.-C. Lin, Macromolecules 2005, 38, 5400.
46. C. M. Silvernail, L. J. Yao, L. M. R. Hill, M. A. Hillmyer, W. B. Tolman, Inorg. Chem. 2007, 46, 6565.
47. Y. D. M. Champouret, W. J. Nodes, J. A. Scrimshire, K. Singh, G. A. Solan, I. Young, Dalton Trans. 2007, 4565.
48. Tin-based systems: H. R. Kricheldorf, M. V. Sumbél, I. Kreiser-Saunders, Macromolecules 1991, 24, 1944.
49. H. R. Kricheldorf, S.- R. Lee, Macromolecules 1996, 29, 8689.
50. H. R. Kricheldorf, S. Eggerstedt, Macromol. Chem. Phys. 1998, 199, 283.
51. S. Penczek, A. Duda, A. Kowalski, J. Libiszowski, K. Majerska, T. Biela, Macromol. Symp. 2000, 157, 61.
52. A. Kowalski, J. Libiszowski, A. Duda, S. Penczek, Macromolecules 2000, 33, 1964.
53. Lanthanides, rare-earth metal-based systems: F. M. Kerton, A. C. Whitwood, C. E. Willans, Dalton Trans. 2004, 2237.
54. M. Yamashita, Y. Takemoto, E. Ihara, H. Yasuda, Macromolecules 1996, 29, 1798.
55. Y. Shen, Z. Shen, Y. Zhang, K. Yao, Macromolecules 1996, 29, 8289.
56. O. Coulembier, P. Degée, J. L. Hedrick, P. Dubois, Prog. Polym. Sci. 2006, 31, 723.
57. See for example: C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217.
58. V. C. Gibson, C. Redshaw, G. A. Solan, Chem. Rev. 2007, 107, 1745.
59. G. Droogmans, C. Maertens, J. Prenen, B. Nilius, Br. J. Pharmacol. 1999, 128, 35.
60. M. J. Colston, H. C. Hailes, E. Stavropoulos, A. C. Hervé, G. Hervé, K. J. Goodworth, A. M. Hill, P. Jenner, P. D. Hart, R. E. Tascon, Infection. Immunity 2004, 72, 6318.
61. J. Sun, D. Wang, R. K. Jain, A. Carie, S. Paquette, E. Ennis, M. A. Blaskovich, L. Baldini, D. Coppola, A. D. Hamilton, S. M. Sebti, Oncogene 2005, 24, 4701.
62. A.W. Coleman, S. Jebors, S. Cecillon, P. Perret, D. Garin, D. Marti-Battle, M. Moulin, New J. Chem. 2008, 32, 780.
63. R. Lalor, H. Baillie-Johnson, C. Redshaw, S. E. Matthews, A. Mueller, J. Am. Chem. Soc. 2008, 130, 2892.
64. D. M. Homden, C. Redshaw, Chem. Rev. 2008, 108, 5086.
65. M. Giusti, E. Solari, L. Giannini, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1997, 16, 5610.
66. V. Esposito, E. Solari, C. Floriani, N. Re, C. Rizzoli, A. Chiesi-Villa, Inorg. Chem. 2000, 39, 2604.
67. E. Zeller, S. Koenig, U. Radius, Inorg. Chim. Acta 2004, 357, 1813.
68. A. Ali, S. Salunke-Gawali, C. P. Rao, J. Linares, Inorg. Chem. Commun. 2004, 7, 1298.
69. M. M. Olmstead, G. Sigel, H. Hope, X. Xu, P. P. Power, J. Am. Chem. Soc. 1985, 107, 8087.
70. J. Zeller, S. Koenig, U. Radius, Inorg. Chim. Acta 2004, 357, 1813.
71. A. E. J. Wetherby, L. R. Goeller, A. G. DiPasquale, A. L. Rheingold, C. S. Weinert, Inorg. Chem. 2007, 46, 7579.
72. U. Desroches, G. Pilet, P. A. Szilagyi, G. Molnar, S. A. Borshch, A. Bousseksou, S. Parola, D. Luneau, Eur. J. Inorg. Chem. 2006, 357.
73. D. Jacoby, C. Floriani, A. Chiesivilla, C. Rizzoli, J. Chem. Soc. Dalton Trans. 1993, 813.
74. S. F. Chin, M. Makha, C. L. Raston, M. Saunders, Chem. Commun. 2007, 1948.
75. D. M. Kurtz, Chem. Rev. 1990, 90, 585.
76. J. L. Atwood, P. C. Junk, S. M. Lawrence, C. L. Raston, Chem. Commun. 1996, 15.
77. M. G. Gardiner, S. M. Lawrence, C. L. Raston, B. W. Skelton, A. H. White, Chem. Commun. 1996, 2491.
78. E. Bukhaltsev, I. Goldberg, A. Vigalok, Organometallics 2004, 23, 4540.
79. N. Kotzen, I. Goldberg, A. Vigalok, Inorg. Chem. Commun. 2005, 8, 1028.
80. E. Bukhaltsev, L. Frish, Y. Cohen, A. Vigalok, Org. Lett. 2005, 7, 5123.
81. C. Liu, F. Luo, Y. Bi, W. Liao, H. Zhang, J. Mol. Struct. 2008, 888, 313.
82. N. Kotzen, I. Goldberg, A. Vigalok, Organometallics 2009, 28, 929.
83. C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, 1989.
84. D. M. Roundhill, Prog. Inorg. Chem. 1995, 43, 553.
85. C. Wieser, C. B. Dieleman, D. Matt, Coord. Chem. Rev. 1997, 165, 93.
86. A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713.
87. C. D. Gutsche, Calixarenes Revisited, Royal Society of Chemistry, Letchworth, 1998.
88. J. L. Atwood, L. J. Barbour, M. J. Hardie, C. L. Raston, Coord. Chem. Rev. 2001, 222, 3.
89. J. L. Atwood, L. J. Barbour, M. J. Hardie, C. L. Raston, Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer, Dordrecht, 2001.
90. C. Floriani, R. Floriani-Moro, Adv. Organomet. Chem. 2001, 47, 167.
91. W. Sliwa, Croat. Chem. Acta 2002, 75, 131.
92. P. D. Harvey, Coord. Chem. Rev. 2002, 233/234, 289.
93. C. Redshaw, Coord. Chem. Rev. 2003, 244, 45.
94. F. A. Cotton, L. M. Daniels, C. Lin, C. A. Murrillo, Inorg. Chimica Acta 2003, 347, 1.
95. A. J. Petrella, C. L. Raston, J. Organomet. Chem. 2004, 689, 4125.
96. P. D. Hampton, C. E. Daitch, T. M. Alam, Z. Bencze, M. Rosay, Inorg. Chem. 1994, 33, 4750.
97. C. E. Daitch, P. D. Hampton, E. N. Duesler, Inorg. Chem. 1995, 34, 5641.
98. M. Hinrichs, F. R. Hofbauer, P. Klufers, M. Suhanji, Inorg. Chem. 2006, 45, 6688.
99. C. Redshaw, M. A. Rowan, L. Warford, D. M. Homden, A. Arbaoui, M. R. J. Elsegood, S. H. Dale, T. Yamato, C. P. Casas, S. Matsui, Chem. Eur. J. 2007, 13, 1090.
100. C. Redshaw, M. Rowan, D. M. Homden, M. R. J. Elsegood, T. Yamato, C. Perez-Casas, Chem. Eur. J. 2007, 13, 10129.
101. B. Masci, P. Thuery, Supramol. Chem. 2003, 15, 101.
102. J. Ling, Z. Shen, W. Zhu, J. Polym. Sci. A 2003, 41, 1390.
103. Y. K. Gun'ko, U. Cristmann, V. G. Kessler, Eur. J. Inorg. Chem. 2002, 1029.
104. A. W. Addison, T. N. Rao, J. Reedijk, J. Van Rijn, G. C. Verschoor, J. Chem. Soc. Dalton Trans. 1984, 1349.
105. W. Clegg, M. R. J. Elsegood, S. J. Teat, C. Redshaw, V. C. Gibson, J. Chem. Soc. Dalton Trans. 1998, 3037.
106. G. D. Andreetti, G. Calestani, F. Ugozzoli, A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, J. Incl. Phenom. Macro. Chem. 1987, 5, 123.
107. A. Arbaoui, C. Redshaw, D. L. Hughes, unpublished results. The unit cell is a=16.246(3), b=16.269(4), c=17.439(2), α=77.821(16), β=69.341(14), γ=88.906(17), volume=4208.0(14), Z=1, Triclinic, P-1 (No. 2).
108. V. C. Gibson, C. Redshaw, M. R. J. Elsegood, J. Chem. Soc. Dalton Trans. 2001, 767.
109. G. E. Hofmeister, F. E. Hahn, S. F. Pedersen, J. Am. Chem. Soc. 1989, 111, 2318.
110. J. M. Veauthier, W. S. Cho, V. M. Lynch, J. L. Sessler, Inorg. Chem. 2004, 43, 1220.
111. I. Siewert, C. Limberg, S. Demeshko, E. Hoppe, Chem. Eur. J. 2008, 14, 9377.
112. M. Parvez, G. L. BergStresser, H. G. Richey, Acta Crystallogr. Sect. C 1992, 48, 641.
113. Q. Xu, M. Du, Y.-M. Guo, X.-H. Bu, Acta Crystallogr. Sect. C 2001, 57, 893.
114. C. K. Williams, N. R. Brooks, M. A. Hillmyer, W. B. Tolman, Chem. Commun. 2002, 2132.
115. Z.-F. Chen, S. Kang, S.-M. Shi, B. F. Abrahams, H. Liang, J. Mol. Struct. 2008, 882, 134.
116. O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147.
117. E. Bukhaltsev, L. Frish, Y. Cohen, A. Vigalok, Org. Lett. 2005, 7, 5123.
118. A. Arduini, A. Casnati in Macrocycle Synthesis (Ed.: D. Parker), Oxford University Press, 1996, chap. 7.
119. B. Masci, J. Org. Chem. 2001, 66, 1497.
120. B. Dhawan, C. D. Gutsche, J. Org. Chem. 1983, 48, 1536.
121. Despite repeated elemental analyses for 3, 4, there was no fit between experimental % carbon values, % carbon theoretical values.
122. SMART (1997 & 2001), SAINT (2001 & 2008), APEX 2 (2008) software for CCD diffractometers. Bruker AXS Inc., Madison, USA.
123. G. M. Sheldrick, SHELXTL user manual, version 6.10. Bruker AXS Inc., Madison, WI, USA, 2000.
124. R. W. W. Hooft, COLLECT data collection software, B. V. Nonius, 1998.
125. Processing of XRD data collected in oscillation mode: Z. Otwinowski, W. Minor, Macromol. Crystallogr. A 1997, 276, 307 -326.
126. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112 -122.
127. A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, C34.